Which Season of ‘The Sopranos’ Is the Best … and Which Deserves To Be Whacked?

Asking many fans to choose their favorite season of The Sopranos is like asking them to pick their favorite child. Challenge accepted!

The HBO drama about a New Jersey crime family premiered January 10, 1999 and ran for six seasons until June 10, 2007. The beloved series is considered by many to be one of the most influential TV shows of all time, even receiving credit for kicking off the Second Golden Age of Television, a period known for its high number of prestigious and acclaimed shows. The series premiered over 25 years ago, yet it’s still widely discussed (and criticized) as if it just aired last week.

David Chase created the show, which centers around mob boss Tony Soprano (James Gandolfini) as he struggles to overcome his anxiety with help from his long-suffering therapist Dr. Jennifer Melfi (Lorraine Bracco). Tony has a lot of stress in his life; he’s balancing a growing mafia business that’s constantly under attack from both inside and outside forces (not to mention the Feds), and he’s also trying to be a husband to wife Carmela (Edie Falco) and a father to his kids, daughter Meadow (Jamie-Lynn Sigler) and son AJ (Robert Iler).

If you’ve never watched a single episode, you should start from season 1 and watch the whole thing straight through. However, fans like me, who watched the show air live each week back in the day and have since rewatched the series multiple times … we like to mix things up! Below you’ll find my ultimate ranking of each season of The Sopranos, with my favorite season of them all in the number 1 spot.

6. Season 6 (2006)

The final episode is epic and extraordinary, I’ll give you that. But other than the very last episode, the sixth and final season was not nearly as much fun to watch as the others. Uncle Junior (Dominic Chianese) is fully senile and accidentally shoots Tony. New York boss Johnny Sack (Vince Curatola) is humiliated and disgraced, and henchman Vito (Joseph R. Gannascoli) gets whacked by Phil Leotardo’s (Frank Vincent) guys just because he’s gay. The fact that Phil overstepped his bounds and did what Tony refused to do (whack Vito) further escalates the simmering tension between the New York and New Jersey families.

The subplot with Chris (Christopher Moltisanti) going to Los Angeles to become a screenwriter is tedious and feels superfluous. In fact, Chris is such a perpetual screw-up that by the time Tony has had enough of his mentee’s B.S., we almost feel relieved to be done with him, too. Dr. Melfi drops Tony as a patient, AJ is miserable, and many of our favorite characters meet a grisly end. The whole season is just, to be honest, a major bummer. And then we get the biggest bummer of them all.

5. Season 1 (1999)

The first season is the least polished of all, yet it was that very rawness that drew us all in. Audiences were immediately enthralled by the idea of a regular schlubby guy like Tony leading a not-so-secret double life as a career criminal. The juxtaposition of loving family man and violent mobster is a fascinating character study, especially with added insight from Dr. Melfi.

Still, most of this season is setting up action for the future story and getting to know the individual players. This means a few of these slow burn episodes are, to be frank, a tiny bit boring. We also have to sit through scenes featuring Tony’s awful, hate-filled mother Livia (Nancy Marchand), which is difficult. What kind of mother puts out a hit on her own son? The same kind that raises a killer like Tony, it seems.

Season 1 is still great, but it’s just a launchpad for what’s to come!

4. Season 4 (2002)

So much happens in this season, and we gain a deeper understanding of what makes Tony tick. Ralph “Ralphie” Cifaretto (Joe Pantoliano) is back this season, and he’s an obnoxious and untrustworthy henchman whose mouth gets him in hot water with the NY crew. Christopher’s heroin addiction finally catches up with him, and Tony engages in a risky affair with a woman he met in his therapist’s waiting room.

While we enjoy seeing the dealings between the two mob families, we don’t love watching Tony and Carmela separate. Also, watching poor Adriana (Drea de Matteo) make a friend who turns out to be an undercover FBI agent, then get roped into informing on the family, just does not feel good. She gets sicker and sicker as the worry eats away at her, and as a viewer, we can feel that unpleasant tension. A bright spot in the season is the “Pie-O My” episode when Tony once again shows us his tender side … right before he becomes so enraged that he kills Ralphie with his bare hands.

3. Season 5 (2004)

Season 5 is when everything starts heating up, and it’s a ton of fun to watch the action hit the boiling point. It starts with a bunch of mobsters getting released from prison, including Tony’s cousin and childhood friend Tony “Tony B.” Blundetto (Steve Buschemi). Tony B. is determined to stay straight, but of course he’s quickly drawn back into a life of crime. Meanwhile, a war is brewing inside the New York crew, which spills over into Tony’s orbit.

The best part of this season, however, is watching Adriana fall further down the rabbit hole with the Feds. In the end, she goes for a ride upstate and “enters witness protection,” but we all know what that means.

2. Season 3 (2001)

Ralphie tries to step into the shoes of Richie Aprile (David Proval), who “went missing” … but was actually murdered by Tony’s sister Janice (Aida Turturro) in one of the most satisfying scenes in television history. He’s a good earner, but Ralphie lacks tact and has a high sense of entitlement, which gets him in trouble with Tony. After Ralphie kills his girlfriend, a sweet dancer at the Bada Bing, Tony beats him up in front of everyone, and the tension cranks up even further.

Dr. Melfi is sexually assaulted and gets no help from police, raising interesting feelings about whether it’s ethical to let Tony handle things his own way. Meadow dates Jackie April Jr. (Jason Cerbone), who quickly goes off the rails because he’s just not very smart. Everything is starting to fall apart in Tony’s world. Even the impeccably-coiffed Paulie Walnuts (Tony Sirico) loses his cool in the season’s best episode, “The Pine Barrens.”

1. Season 2 (2000)

We saved the best, which is the second, for last! This is when we get to see Janice take out her abusive boyfriend Richie, Tony finally has it out with his evil mother, and Tony and Junior’s rift comes to a head.

This is also the season in which Tony’s right-hand man, Salvatore “Big Pussy” Bonpensiero (Vincent Pastore), starts ratting to the Feds, which catches up to him. It’s the first time we’ve watched Tony and the crew take out one of their own in such a personal manner. It’s not a job they relish; it’s just a necessary part of business. A subplot involving Christopher and some low-level crooks named Bevilacqua and Gismonte kicks off plot points that will endure throughout the series.

Season two is the season that hooked many of The Sopranos’ most ardent fans. It’s packed with action and emotion, and the people who get whacked actually deserve it. Satisfying from start to finish!

All episodes of The Sopranos are currently streaming on Max.